


Got Something To Chauffeur This Night

by hollyblue2



Category: Supernatural
Genre: Alternate Universe, Alternate Universe - Modern Setting, Charity Gala, Chauffeur!Dean, Class Divide, Fake/Pretend Relationship, Fluff, M/M, Minor Angst, Valentines Promptus Exchangarama, businessman!cas, dick is a dick, smarmy bosses
Language: English
Status: Completed
Published: 2020-02-14
Updated: 2020-02-14
Packaged: 2021-02-22 16:09:24
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 5,627
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22718683
Author URL: https://archiveofourown.org/users/hollyblue2/pseuds/hollyblue2
Summary: Dean is just a chauffeur... and also a fake date for his favourite client, Castiel Novak. Pie was on offer, and Dean will do anything for pie and Castiel.
Relationships: Castiel/Dean Winchester
Comments: 32
Kudos: 317
Collections: Promptus Exchangarama





	Got Something To Chauffeur This Night

**Author's Note:**

  * For [heylittleangel](https://archiveofourown.org/users/heylittleangel/gifts).



> You may be surprised, but I am not dead. This is my first fic of the year and it's for Valentines Day and also Gii! 
> 
> Written for the Writers of Destiel Valentines Fic Exchange. I chose their second prompt (which is in the end notes) so I hope you all enjoy this bit of floof, especially you Gii!
> 
> Beta'd by @galaxystiel ^_^
> 
> Happy Valentines Day, everyone! ♥♥

* * *

Dean brings the Lincoln Town Car to a slow halt when he reaches the gate to the Novak residence before winding down his window and pressing the button to speak.

"Eight AM car for C. Novak," Dean announces. The speaker crackles for a moment and then there's a distinct buzz as the gates begin to open. 

He's met, as always, with the two storey home that projects how wealthy the residents are inside without hesitation. It's mostly daylight now so the outside lights are off and a few of the curtains are open, showing lights on inside the house. He can't see any movement, but his arrival has been announced so likely his passenger is heading out of the door. 

It's one of the things he likes about C. Novak. He's always punctual. The rest of his family, not so much. The amount of times he's had to wait nearly half an hour for Z. Novak to step in to the back of his car is innumerable and he's only been working for them for three years.

Briefly lost in his thoughts, Dean only realises that Castiel has left the house when he hears the back door open. 

"Morning, Mr. Novak," Dean greets, twisting in his seat a little and watching as he slides across to sit diagonally from Dean and buckling himself in. Dean hears him sigh loudly and sees him close his eyes before opening them and looking straight at Dean.

"Please, for the last time, call me Castiel," Castiel says with a smile. 

"Alright, Cas," Dean replies, using the only nickname Castiel hasn't complained about. "How are you this morning?"

"Tired, and I didn't have time to make myself a coffee." 

"Didn't you get the butler to make it?" Dean teases, putting the car in gear and easing out of the driveway and back onto the quiet road that leads up to the Novak house. 

"We don't have a butler," Castiel says and Dean sees him frown in the rearview mirror. 

Dean checks the time on his watch—8:11am—and realises that they have time to stop at a coffee place if Cas wants to. "We can stop at The Honeycomb, if you want."

"Ooh, please, if you don't mind." He watches Cas light up at the idea and it makes Dean happy in turn.

"Anything for you," Dean says with a smile and indicates to pull off the main highway and into the small town just off it. The coffee shop isn't far away, and it's run by one of Dean's close friends so he knows the quality of the coffee is great and their sweet treats just as much. 

Dean pulls up into the parking lot and is about to get out when Castiel halts him. "On me," he says and he's out of the car, trenchcoat billowing behind him in the breeze. 

He waits, tapping his fingers on the steering wheel and absorbing himself in the people around him. Some people look at the car, knowing that it's not the average vehicle and Dean preens a little. He doesn't work nearly as hard on this vehicle as he does his  _ baby  _ but he makes sure she runs smoothly and shines like a gem, especially when he's running Castiel around. 

Castiel comes back out, and Dean is delighted to see two to-go cups in Castiel's hands. The guy is endlessly thoughtful. 

"One coffee as black as hell for you, and a vanilla latte for myself. Oh, and I got their honey and lemon cake again." The smell of coffee wafts through the vehicle and Dean takes a long inhale at his own, knowing it'll be too hot to drink at least until the rejoin the highway. The route to Castiel's office is one he makes frequently, so he's learnt the patterns by heart. 

Dean's stomach rumbles and he masks it with a cough but it doesn't get past Castiel which is clear when he says, "Benny added a slice of pie for you. Cherry, he said."

"Hell yes!" Dean whoops, breaking his usual formal demeanor. 

"So I was wondering…"

"Oh no," Dean swallows, looking in the mirror at Cas before focusing back on the road, overtaking a slow car and then pulling back in again. "I mean, I'll do anything for that slice of pie, but 3am pick-ups aren't my favourite." 

"It's … more than that, a huge favour and I didn't know who else to ask." 

If it's not a middle of the night pick up after one of Castiel's friends parties, then he has no idea what could be more than that. He never minds a drunk Cas in the back of his car, but he definitely minds his friends, they're loud and obnoxious and don't respect for what he's doing for them, not like Cas does. 

"What do you need?"

"There's a charity gala on the fourteenth which I'm expected to attend but I need a, um… date." 

Dean slows down to a stop at an intersection. "You want me to find you a date for Valentine's Day? You know you could probably look on Tinder right? And I bet that chick that I see in my car after a 3am pick-up would take you up on the offer if you asked her," Dean suggests and then takes a sip of his coffee, perfectly temperate. 

Castiel goes quiet for a moment. The rumble of the engine is the only sound. Dean should really remember to put music on while Castiel is in the car, he knows the guy won't mind.

"I was going to ask you," Castiel says and then proceeds to shove an over-large bite of cake into his mouth. 

Dean tries to wrap his head around what Castiel has just asked of him. "So let me get this straight, you want to hire me to be your date to a Valentines party?" 

"Charity gala, for the American Heart Association," Castiel corrects as if it explains himself. 

"I think you owe me that pie, now." 

"There's no one else to ask. Meg is married, and the other board members know she is, so we can't even fake it for the evening. I can't show up to a work event without a date on Valentines day." 

"I did say I would do anything for that pie." 

Dean's stomach rumbles again as the pie is passed over the seat and onto the empty passenger seat. 

"So you'll come—with me?"

"Yeah, just for you. You're lucky I'm not booked out for that night, and it’s not like I have anything else to do except eat pizza and watch old westerns," Dean says, scrolling quickly through the calendar on his phone and finding the night of Valentines Day blissfully blank. His phone then buzzes and an alert pops up with a new job. 

**_Friday February 14th - C.Novak 7pm pick up. Location to: Garrison Offices._ **

"Thanks," Dean says with a chuckle. He concentrates on the road for the last few miles, before pulling up at Cas' office. "I'm down to pick you up at ten-thirty," Dean tells him and Castiel nods, stepping out of the car. 

"Thank you for the ride," Castiel says. He's the only one who ever thanks him, everyone else assumes that because this is his job, he doesn't need to be thanked. He never expects it, but it is always nice to hear. "And for agreeing to be my fake date, I know it's probably… uncouth."

"Uncouth," Dean repeats and laughs. "Go do your job and spout fancy words as them. I'm just your driver—and fake date." 

"Wear your best suit!" Castiel calls back as Dean begins to drive away, his window winding up. He gives Castiel a thumbs up and heads back into the highway towards his apartment. 

As soon as he's around the corner, out of sight of the office Cas works at, Dean turns up the rock music. This was a bad idea to agree to, but then again, it’s Castiel Novak and he  _ likes _ the guy. 

"Fuck!"

***

Dean stands in front of the mirror, trying to fix his black tie before sighing and ripping it off, throwing it onto the bed behind him. He picks another tie up, this one burgundy and tries that one. He's still not satisfied and finally picks up the red tie from the drawer. This one doesn't look so bad, and Castiel did suggest he wear a red  _ something _ . 

Mostly happy with his appearance, his hair gelled and swept up neatly, parted to one side in a style he very rarely bothers to do, and his suit pressed immaculately—courtesy of the dry cleaners at the end of the block. 

He grabs his keys and wallet and heads down the elevator to the garage. He pays for a second spot in the underground apartment parking lot, one for his personal car, a 1967 Chevrolet Impala which he loves dearly, and the other for his work car, a 2014 Lincoln Town Car. He wonders briefly if he should take his baby, but then remembers that he's technically supposed to be working and decides against it.

"Sorry, baby, I promise you a drive tomorrow," he whispers, and pats her hood before unlocking the Lincoln and sliding into the seat. 

Headlights on, engine on, Dean tries to calm himself down before moving off. He's given himself plenty of time to turn up at Castiel's, figuring he'd panic somewhere along the way. He agreed to this, and he's damn well going to follow through. Being someone's fake date is not what he signed up to do, but he'll make sure he does a good job of it. 

He has to admit that Castiel is probably the only person he'd ever do it for. His other clients are more obnoxious and barely treat Dean like a human being, often pretending he's not there. The only gratitude being that he gets paid decently. 

Castiel though, he can chat to him freely, can drop most of the formalities he often upholds with clients and he knows a fair bit about him. While Castiel is an upstanding member of his family and the company he works for, Castiel isn't shy about his hobbies—an apiarist and an amateur artist—of which his family do not approve of. They're not social enough, is what Castiel says they complain about. 

Through all Dean's thinking about Castiel, he realises he's got to the Novak household on autopilot and is idling at the gate. 

"Here goes then," he says to himself and winds down his window to press the speaker button. "7pm car for C. Novak." 

The gate opens and Dean finds himself crawling towards the house. He's nervous, has been ever since Cas suggested he be his fake date, but now he feels  _ extra _ nervous. 

Dean does feel an attachment to the guy, he doesn't dare call it anything more, he is a client and just so happens to be the one person who speaks to him most and who he feels he can share with the most. That doesn't mean that he's going to be anything more. Tonight is just another job, granted out of his remit, but just another job all the same. This isn't going to change anything between them.

Dean glances over at the clock in the car—7:03pm—and realises that Castiel is late. Very unusual. Maybe he backed out… Dean checks through his client notifications and finds that the job is still booked in for the entire night. 

7:06pm and Castiel is still not here. Dean's stomach churns and his leg rumbles up and down as the engine idles. He does his best not to look at the clock any more, to calm himself down, but finds it nearly impossible and ends up staring the numbers down. 

At 7:09pm, Dean hears a noise outside and finds Castiel dashing out of the door, a tie in his hand and patting down his pockets trying to check he has everything. He's a whirlwind but as soon as he catches Dean's eye, Castiel seems to slow down.

Castiel is still fiddling with his tie so steps out of the car to help him. “Here, let me.”

Castiel stops, looking up at Dean, his blue eyes shining in the light from the house. Dean slides Cas’ red tie through the collar of his shirt and ties it in a half-Windsor knot, just like he does every morning for himself, and then adjusts it until it sits neatly at Cas’ collar.

“Thank you.”

“Don’t sweat it,” Dean says with a smile and turns back to the car. 

Dean expects him to climb in the back like normal, but then watches with anticipation as Castiel walks around the front of the car and opens the passenger side door. 

"Good evening," Castiel says with a small smile and buckles himself in. 

"Hey," Dean replies, still a little bewildered and it must show blatantly on his face.

"I figured the back seat would feel awkward if we're supposed to arrive together as a couple."

"No, yeah, that's fine Cas. Just… never thought it would be the case. Ready?" Dean nods to Cas, who nods right back at him. "Let's get this show on the road."

The drive is quiet, Dean parts his lips several times to say something but then doesn't. He has a few questions he needs to ask Cas about tonight, to make sure they have some kind of story and maybe learn a bit about who's going to be there and why the hell he needs a hired date anyway, and why Cas chose  _ him _ to say the least. 

The whole, ‘them both being guys’ thing doesn't really mean a lot, nor shock him. He's seen Cas on an occasion or two wrapped up in the arms of another guy that was clearly a not just friends situation, so Castiel liking men was sort of obvious from the start. 

Dean, too, hadn't exactly hid the fact that he was bisexual—perhaps to unknowing eyes he wasn't exactly out, but to those that knew it was almost obvious. He had two adjoining arrows tattooed on his wrist fading from pink, into purple, and then blue by the time it got to the other arrow. It often peeked out from under his shirt sleeves. It was proof, to himself above anyone else, that he was happy with who he is—finally.

Tightening his fingers around the steering wheel, Dean finally speaks. "What do you need me to do tonight?" 

"Hang around, small talk, generally just… pretending to be like my boyfriend or something."

"Uh-huh…" Dean chews it over. A boyfriend is something he's never had, and he never counted his six-day fling with Aaron back in high school. It may have meant something back then, but not now, not in the same way he needed it to. "Who are you trying to impress… or I dunno, make uncomfortable? There's gotta be a reason you picked me over someone else."

"Ah, oh. My, um, an old boss of mine, and current board member, from before my father passed the company onto my shoulders. He was very much a dick to me when he found out that I wasn't straight. It wasn't a big deal to me, but he got it in his head that it was a reason I wasn't suitable for promotion and he'd pass up on my application every time. I couldn't prove it, but I quit anyway. My father was furious. I went to work for him instead, and to be honest, I much preferred working for my dad than Dick Roman."

"With a name like that, he already sounds like a dick." 

Castiel laughs, and Dean takes the moment to glance over at him. His shirt is still open at the collar, two buttons undone and the beginnings of crinkles around his eyes. His dark hair is vaguely tidy, in a very Castiel kind of way, and he's running the tie he's holding between his fingers.

"And I picked you because even though you get paid to drive me around, you're the one I feel most comfortable with. It’s stupid, really, and I should probably have told you that before."

"Thanks for telling me now," Dean says sincerely. "Do we need some kind of story tonight?"

"I doubt people will ask too many questions, I'm happy for you to be yourself. I guess we fell in love on our weekly car journeys." 

***

The party is already in the swing of it by the time they arrive. Dean reluctantly gets out of his car and hands his keys to the valet, it's only when Castiel takes Dean's arm, does Dean tear his eyes away from his car.

"Your car will be fine, and if it isn't, I will reimburse you for the damages." It doesn't help, but he tries his best to put it out of his mind anyway. 

They ride the elevator, blissfully on their own, up to the top floor where the main event is happening. It gives Dean a chance to feel comfortable with Castiel, their arms looped together. It feels strange and yet, somehow, like something they've been doing forever. 

The elevator pings and Dean snatches a glance at Castiel, only to find the other man looking at him. Dean's knees feel a little weak in that moment and he wonders if this is really a good idea.

Dean's strength comes back to him as Castiel moves forward. 

"We just need to make this believable," Castiel whispers close to his ear.

"I can do that, sweetheart," Dean replies and he watches with satisfaction as Castiel's cheeks tinge with pink. 

There's soft music playing in the background of the large hall on the top floor. Chairs and tables are set up just outside of a stage and podium. Not many people are sitting down, most mingling with other guests and colleagues. 

"Hey, let me guess who your smarmy board member is?"

He hears Castiel chuckle as he begins to scan the room. He picks out a couple of people to shortlist: a stout looking man, wearing a dark suit and a red patterned tie, with a long stubble and hair that seems too messy. It's the man's chuckle as he speaks to several people around him that makes Dean wonder about him. 

Another man is taller, with brown hair parted and well kept, his face looks young from a distance and he wears a blue suit with a red tie. The constant ugly smirk on his face suddenly tips Dean off. 

"Him?" Dean asks, discreetly pointing in the second man's general direction. "Ten o'clock, talking to the three men?"

"Yeah, that's him."

"Oh boy. He really  _ is _ smarmy. That smirk is gross." Dean huffs and then turns his back to him. "Anyone here you do want to speak to?"

"Yes, I'd like to introduce you to one of my friends. I don't think you've met her before. She doesn't attend the parties I've been to."

They make their way across the room, Dean sticking close by Castiel's side. He feels out of place here for definite, like a fake amongst everyone else. Even the wives and husbands of the other employees seem to be of the same social standing as Castiel and their other halves. Dean is just some low level driver. 

"Dean, this is Charlie Bradbury, technical analyst," he introduces. 

The redhead waves and smiles brightly at him. "Just a fancy title for me making sure his powerpoints don't get fucked up."

Dean nods and smiles back. "I'm…" Dean hesitates for a second.  _ Just be yourself _ , Castiel had said. "I'm a chauffeur."

"Cool! Hey, so Star Trek or Star Wars?"

"Star Wars," Dean replies with a smile. He likes Charlie already. 

"Oh God," Castiel grumbles next to him and Dean can't help laughing and elbowing him in the side. 

"Who shot first?" 

"Han, no doubt about it," Dean says without hesitation. 

"Castiel, I like him." 

"Hey, you hear that, she likes me!"

Castiel groans and rolls his eyes. "Charlie's lucky I'm hopeless at anything tech-related." 

Dean finds it easy to get sucked into the conversation with Castiel and Charlie. He likes this Castiel the most—apart from the one who ends up in the back of his car—he's carefree, smiling and relaxed and even though he's not enthused for the topic, he's joining in anyway. He was expecting Castiel to change into some stuck up businessman, but he's been anything but. 

"Uh oh, time for me to not exist. Gross Dick incoming. Bye." Charlie disappears into nothing and then suddenly Dick Roman has wedged himself between where Dean and Castiel had been standing shoulder-to-shoulder.

"Mr. Novak, it's nice of you to show your face," he says and the tone of his voice sets Dean on edge right away. 

"I'm here for the charity donation, Mr. Roman. Of course I'm here," Castiel retorts; and there's the straight-laced businessman voice Dean had been expecting all night. 

"And you haven't introduced me to your friend?" Dick's smirk is turned on him. "Who might you be?" 

"Dean, I'm his boyfriend." Dean's decision to announce that surprises him just as much it does Dick. He nods briefly and turns his attention back to Castiel.

“So, you’ve brought your boyfriend along?” 

“Yes,” Castiel replies and Dean can see that wary look in his eye. 

Dick turns a scrutinising eye on Dean, and he can feel him looking him up and down. Dean shifts uncomfortably, realising that Dick can probably sense that he’s not the usual kind; and he’s right.

“He’s not exactly  _ our sort _ , is he? Surely you could have done better than him?”

Dean didn’t know what to expect with regards to the man’s opinion of him, but it certainly wasn’t that. Dean glowers and he bites his lip not to say anything rude. He won't act like a dick, not in front of them. He does his best to hide how much those words hurt and instead directs his glare right at Dick instead. He’s not the same as them, he’s not even Castiel’s boyfriend, but nonetheless it still stings something deep inside him. 

“Richard.” The warning comes low, and with an unimpressed eyebrow. 

“I mean, look at him…” Dick gestures to Dean and Dean feels his body tense. The guy deserves to be punched in the face, but he knows that, for Castiel’s sake, that is not the thing to do. Dean drowns him out, staring over at the busy bar and watching as the bartender hands out drinks to the guests. He tunes back in at the wrong moment, hearing, “You should have kept hold of that pretty girl, Hannah. She was so much better.” 

Dick insists on hanging around for much longer than Dean can tolerate, and the entire time he makes sure to stand between them both, even as Dean tries to inch back towards Castiel. He feels exposed and shut out and can only grasp onto warmth when Cas’ eyes meet his own briefly. 

Words are on the tip of Dean’s tongue for several minutes. Dick is describing his last work trip somewhere west, playing golf and other non-work things; they also talk about some big board meeting they both attend and it’s then that Castiel seems to have the upper hand in the conversation. Castiel does try to keep Dean included in the conversation, but Dean largely ignores most of it when Dick butts in and steers the conversation away once again.  _ Asshole _ . 

Again and again, Castiel tries to keep Dean in the conversation, and eventually Dean tries to answer with his opinion, only to be shunted out. Inside he's seething, and he needs to get away from the conversation before he does something he regrets. With Castiel speaking more confidently towards Dick, Dean finds the confidence in himself to reach for Castiel. 

He interrupts him mid-sentence. “Sorry, Cas, did you want a drink or anything?”

Castiel smiles, as if he were grateful for the interruption. “Please, Dean, just whatever you’re having.” Dean feels Castiel squeeze his forearm and Dean nods and slips away from them. 

As soon as he’s several steps away from Roman, Dean feels like he’s able to breathe. He finds his way to the open bar and waits his turn. Finally the barman turns his attention to him. Cas said whatever Dean was having, but the man could probably use something strong about now so he grabs him a nice scotch on the rocks, while Dean settles for an apple juice. 

Years ago, this would be high time for a stiff drink, but he gave it all up when he started driving for his job. It had been worth it, and still is except for the occasional moments. He feels better for it too, and had realised he probably drank too much too often. 

When Dean returns to Castiel, the man is blissfully alone. Dick has moved to another group of people and Dean doesn’t have the heart to care anymore. 

“I’m sorry, Dean.”

“It’s fine,” Dean replies, passing the drink to Castiel who takes it gratefully. 

“It’s not—I didn’t bring you here to be insulted.”

“No, just to make people uncomfortable.” Dean takes a long drink of his juice and eyes Castiel as he flounders. 

“Dean,” Castiel withers. He steps forward and in a bold move, takes Dean’s arm with his free hand and holds it tight. 

Dean doesn’t want to talk anymore, he’s decided that he wants to go home, or at least anywhere that isn’t here. This was a bad idea. He doesn’t belong here and everyone knows it. The only thing about him that’s not cheap is his suit and only because he likes to be smart for his job carrying all these big shots around. 

“Dean, I don’t need you to be some upper-class imbecile who cares for no one but himself.” Cas growls with frustration, it's not necessarily directed at him but he still feels it. “I want you to be yourself, okay. That’s the man I like the most.”

The words stun Dean into silence; it’s long enough that Cas pulls him away to a table near the back where they can still see the stage. Their chairs are close, enough that they can talk to each other privately, which is exactly what Dean wants right now. 

“Honestly, Cas…” Dean breathes. “The backseat-you is my favourite too.”

There’s a small smile on Cas’ lips as he ducks his head. Dean can’t  _ see _ the pink tinging the man’s cheeks, but he knows it’s there, especially if his own heated cheeks are anything to go by. He’s sure as heck they’ve both just admitted they like each other, but perhaps not in so many words. 

The light on the stage picks up on the man Dean had almost guessed as Cas’ co-board member, steps up to the podium, and by that Dean realises that he really does step  _ up _ , onto a mini platform, as the man isn’t tall at all. 

“Good evening, everyone. I would like to begin by thanking everyone for the donation from their tickets, the money will be going to the American Heart Association and I’m sure they’ll appreciate it. Next, we will be giving out the awards for the year.”

Dean hardly listens, only catching bits and pieces, clapping at the right moments. At some point, Cas stands and grabs them a refill - another scotch for Cas (a double this time) and another apple juice for Dean. Then Cas stands up, setting his drink down and Dean realises that his name has been called up to the podium. 

Dean claps extra loud, just to be  _ that _ person, and then grins when Castiel looks back to him with mirth. He even chances a glance at Dick Roman, who is less than impressed, perhaps by both Dean and Cas winning the award.

“Congratulations, Mr. Novak, I know this award for board member of the season is highly competitive between yourself and Mr. Roman, and you’ve been voted highest yet again!” 

Another round of applause goes around the room and Dean stands as Castiel swerves back between the tables. When Castiel holds up the glass award, Dean pulls him automatically into a hug. 

It lasts longer than expected, and Dean wonders if he only lets go because he can feel the glass poking into his ribs. 

They stumble apart, laughing gently. “This calls for another drink!” Dean cheers, and gives Castiel’s shoulder a squeeze as he heads back to the bar. 

This time, in a more celebratory fashion, Dean asks for a mocktail, one that comes out a bright peachy orange, and orders Cas another double scotch. He comes back to the table with a grin and hands Cas his drink.

“What on earth do you have?”

Dean takes a slurp of the cold drink. “Virgin sex on the beach.” Dean watches as Cas snickers into his drink. “Hey, I can be childish if I want okay,” Dean retorts. 

“I’m really not surprised, it does look nice though,” Cas says.

“It’s peachy,” Dean tells him. 

They sip their drinks as the awards go on and finally it closes up. By now it’s late and several people make their way around to say goodbye to their colleagues. 

Charlie comes back over to them and Dean is happy to see her. 

“Very nice presentation, Charlie.”

“Of course it was, I made it,” she says with a grin. “Honestly, you’d all be lost without me!”

“There’s just… too many buttons and I can never make it do what I want it to,” Castiel explains, finishing off his drink.

“Are you going home now?” Charlie asks.

Dean slides up closer to Castiel, feeling more comfortable now than he did earlier. 

“Yes, I want to get out of here before we have another run-in with Dick, he was far less pleasant earlier than I expected.”

“Yeah,” Dean agrees quietly, fishing out the orange slice from the bottom of his glass with his straw and eating it. 

“Ugh, that man is gross, I hate working for him.” 

“He told me I can do better than Dean, just because he’s not upper class enough for his taste. Last time I checked, it was  _ my _ choice in men that mattered most.” 

“You got that right,” Charlie grouses, glancing round at Dick Roman and giving her best glare. “I should leave you guys to it, I hope you had a nice night. I need to pack up before I go home.”

“See you soon, Cas. I hope I get to meet you again, Dean.” Charlie waves them off, then Castiel collects his coat. 

“Let’s go.”

The late night air hits Dean as they exit the building and make their way to the valet stand. He hands back his ticket and requests his car, and someone swings it round from the parking lot. It’s all in one piece. Dean tips the valet generously and thanks him, before sliding into the driver’s seat while Castiel gets back into the front passenger seat. 

As they drive off back towards Castiel’s house, Dean can’t help but glance over at him. “You know, as weird as it is, it’s nice having you up front.”

“I like it too, there’s a much better view,” Castiel says and Dean agrees before realising that Castiel is staring at him with a soft expression. He blushes. 

The rest of the journey is a nice, comfortable kind of silence and Castiel’s house comes up too soon. Dean punches in the familiar gate code and drives through. 

“Here you go.”

“Thank you, Dean. I appreciated you coming out with me tonight, and I’m sorry for what Roman said, he had no right to say that. I meant what I said earlier, too. I like you for who you are and not who someone else expects you to be.”

“Thanks, Cas. You don’t have to apologise for him.”

“I feel like I do.”

Castiel turns his whole body to Dean, one leg up on the seat. “Dean…” Dean switches the engine off, sensing a conversation lasting more than a couple of minutes. “I know I asked you to come with me without it being real, but it doesn’t feel fake any more.”

“Cas…” Dean starts, he doesn’t know what to say, not really, and of course seeing more of Castiel in a casual way would be amazing, but it could be disastrous for business. He didn’t work his way into driving for the Novak’s just to lose it all. “I… don’t know.” 

Castiel nods solemnly, and Dean hates that he’s upset him. He likes Cas, he really does and maybe they can make it work, but he won’t stand for being a secret, but making them public has its own issues. 

The other man hesitates as he cracks open the car door, the outside air seeping in and sending a shiver down Dean’s spine. "Would I be terrible to ask if I can kiss you, just once?"

Dean’s heartbeat feels like it skips and speeds up at the same time.

"Just once?" Dean asks, and watches as confusion washes over Castiel's face. Tonight may not have been a perfect night but Dean's not stupid to realise that the past few years building up a friendship with Castiel has been the best thing that’s ever happened to him. He knows that tonight has been a sure show that there’s more between them than just chatting on the way to Castiel’s board meetings, Dick was a dick, but Castiel still cared more about him than anyone else. 

Dean smiles. "Only because I'd like there to be more than one."

**Author's Note:**

> Prompt used: "So, let me get this straight: you want to hire me to be your date to a Valentine's party?"
> 
> I hope you liked this :) 
> 
> [My Tumblr](https://envydean.tumblr.com) | [My Writing Tumblr](https://envydeanwrites.tumblr.com)


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